Simple synthesis of geminal diacetates (Acylals) of aromatic aldehydes

Synthetic Communications

Volumn 36, Issue 9, 2006, Pages 1213-1220

  Rahman, Motiur A F M ^a   Jahng, Yurngdong ^a  

^a Yeungnam University   (South Korea)

Author keywords

Aldehydes; Geminal diacetate; Solvent free conditions

Indexed keywords

ACETOACETIC ACID; ALDEHYDE;

ARTICLE; CATALYST; CHEMICAL REACTION KINETICS; SYNTHESIS;

EID: 33645305158     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910500514154     Document Type: Article

References (53)

1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley: New York, 1999; p. 306.
2. Kochhar, K. S.; Bal, B. S.; Deshpande, R. P.; Rajadhyaksha, S. N.; Pinnick, H. W. Conversion of aldehydes into geminal diacetates. J. Org. Chem. 1983, 48, 1765-1767.
3. Narayana, C.; Padmanabhan, S.; Kabalka, G. W. Cleavage of ethers and diacetates using the boron triiodides-N,N-diethylaniline complex. Tetrahedron Lett. 1990, 31, 6977-6978.
4. Varma, R. S.; Chartterjee, A. K.; Varma, M. Aluminum-mediated deacetylation of benzaldehyde diacetates. A simple deprotection method. Tetrahedron Lett. 1993, 34, 3207-3210.
5. Jin, T. S.; Sun, X.; Li, T. S. A facile and efficient catalyst for deprotection of 1,1-diacetate. J. Chem. Res. Synop. 2000, 128-129.
6. 2O-Nal system. Indian J. Chem. 2002, 41B, 863-864.
7. Reddy, M. A.; Reddy, L. R.; Bhanumathi, N.; Rao, R. K. An efficient biomimetic cleavage of gem-diacetate to aldehydes by β-cyclodextrin under neutral conditions in aqueous medium. Synth. Commun. 2002, 32, 273-277.
8. Sinder, B. B.; Amin, S. G. A synthetic precursor of verruacarin A. Synth. Commun. 1978, 8, 117-125.
9. Gallucci, R. R.; Going, R. C. Reaction of hemiacetal esters, acetals, and acylals with alcohols and acid. J. Org. Chem. 1982, 47, 3517-3521.
10. 3 towards allylic acetals and ethers. Tetrahedron Lett. 1984, 25, 3079-3082.
11. Trost, B. M.; Vercauteren, J. Allylic geminal diacetates. Unusual carbonyl substitutes via metal-catalyzed reactions. Tetrahedron Lett. 1985, 26, 131-134.
12. Sandberg, M.; Sydnes, L. K. The chemistry of acylals. 3. Cyanohydrin esters from acylals with cyanides reagents. Org. Lett. 2000, 2, 687-689.
13. Sydnes, L. K.; Sandberg, M. The chemistry of acylals: Part I, the reactivity of acylals towards Grignard and organolithium reagents. Tetrahedron 1997, 53, 12679-12690.
14. Wegscheider, R.; Späth, E. Addition of acid anhydrides to aldehydes and ketones. Monatsh. Chem. 1909, 30, 825.
15. Knoevenagel, E. Acetylation of organic compounds. J. Liebigs Ann. Chem. 1914, 402, 111-115.
16. Freeman, F.; Karcherski, E. M. Preparation and spectral properties of benzylidene diacetates. J. Chem. Eng. Data 1977, 22, 355-357.
17. 3H. Green Chem. 2002, 4, 255-258.
18. 2 under microwave irradiation. Synth. Commun. 2002, 32, 3469-3474.
19. Ranu, B. C.; Dutta, J.; Das, A. Zinc tetrafluoroborate-catalyzed efficient conversion of aldehydes to geminal diacetates and cyanoacetates. Chem. Lett. 2003, 32, 366-367.
20. Man, E. H.; Sanderson, J. J.; Hauser, C. R. Boron fluoride catalyzed addition of aliphatic anhydride to aldehydes. J. Am. Chem. Soc. 1950, 72, 847-848.
21. Fry, A. J.; Rho, A. K.; Sherman, L. R.; Sherwin, C. S. Cobalt(II)-catalyzed reaction of polycyclic aldehydes and acetic anhydride: Formation of acylals, not 1,2-diketones. J. Org. Chem. 1991, 56, 3283-3286.
22. Michie, J. K.; Miller, J. A. Phosphorus trichlorides as catalyst in the preparation of 1,1-diacetates from aldehydes. Synthesis 1981, 824-825.
23. Deka, N.; Borah, R.; Kalita, D. J.; Sarma, J. C. Synthesis of 1,1-diacetates from aldehydes using trimethylchlorosilane and sodium iodide as catalyst. J. Chem. Res., Synop. 1998, 94-95.
24. 6). Synth. Commun. 2002, 32, 669-673.
25. Yadav, J. S.; Subba Reddy, B. V.; Srinivas, C. Indium trichlorides-catalyzed chemoselective conversion of aldehydes to gem-diacetates. Synth. Commun. 2002, 32, 1175-1180.
26. Yin, Y.; Zhang, Z.-H.; Wang, Y.-M.; Pang, M.-L. Indium tribromide as a highly efficient and versatile catalyst for chemoselective synthesis of acylals from aldehydes under solvent-free conditions. Synlett 2004, 1727-1730.
27. Jin, T.; Feng, G.; Yang, M.; Li, T. An efficient and practical procedure for synthesis of 1,1-diacetate from aldehydes catalyzed by zirconium sulfate tetrahydrate-silica gel. Synth. Commun. 2004, 34, 1645-1651.
28. Scheeren, J. W.; Tax, W. J. M.; Schijf, R. Mixed acylals: Synthesis of alkylidene carboxylate formats. Synthesis 1973, 151-153.
29. 2 under mild condition. Phosphorus, Sulfur Silicon Related Elem. 2004, 179, 19-24.
30. Deka, N.; Kalita, D. J.; Borah, R.; Sarma, J. C. Iodine as acetylation catalyst in the preparation of 1,1-diacetates from aldehydes. J. Org. Chem. 1997, 62, 1563-1564.
31. Karimi, B.; Seradj, H.; Ebrahimian, G. R. Mild and efficient conversion of aldehydes to 1,1-diacetates catalyzed with N-bromosuccinimide (NBS). Synlett 2000, 623-624.
32. 40) as an efficient heterogeneous inorganic catalyst for the chemoselective synthesis of geminal diacetates (acylals) under solvent-free conditions. Tetrahedron Lett. 2003, 44, 3951-3954.
33. Carrigan, M. D.; Eash, K. J.; Oswald, M. C.; Mohan, R. S. An efficient method for the chemoselective synthesis of acylals from aromatic aldehydes using bismuth inflate. Tetrahedron Lett. 2001, 42, 8133-8135.
34. Aggen, D. H.; Arnold, J. N.; Hayes, P. D.; Smoter, N. J.; Mohan, R. S. Bismuth compounds in organic synthesis: Bismuth nitrate-catalyzed chemoselective synthesis of acylals from aromatic aldehydes. Tetrahedron 2004, 60, 3675-3679.
35. Chandra, K. L.; Saravanan, P.; Singh, V. K. An efficient method for diacetylation of aldehydes. Synlett 2000, 359-360.
36. 4-mediated conversion of aldehydes to gem-diacetates. Synlett 2002, 604-606.
37. Karimi, B.; Maleki, J. Lithium trifluoromethanesulfonate (LiOTf) as a recyclable catalyst for highly efficient acetylation of alcohols and deacetylation of aldehydes under mild and neutral reaction condition. J. Org. Chem. 2003, 68, 4951-4954.
38. Reddy, B. M.; Sreekanth, P. M.; Khan, A. Facile synthesis of 1,1-diacetates from aldehydes using environmentally benign solid acid catalyst under solvent-free conditions. Synth. Commun. 2004, 34, 1839-1845.
39. 3, an efficient catalyst for formation and deprotection of geminal diacetates (acylals): Chemoselective protection of aldehydes in presence of ketones. Synlett 1998, 849-850.
40. Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O.; Nocchetti, M. Preparation and deprotection of 1,1-diacetates (acylals) using zirconium sulfophenyl phosphate as catalyst. Tetrahedron Lett. 2002, 43, 2709-2711.
41. 2O). Tetrahedron Lett. 2003, 44, 1301-1303.
42. Olah, G. A.; Mehrotra, A. K. Catalysis by solid superacids: 16, improved Nafion-H-catalyzed preparation of 1,1-diacetates from aldehydes. Synthesis 1982, 962-963.
43. Joshi, M. V.; Narasimhan, C. S. Facile conversion of aldehydes to 1,1-diacetates catalyzed by H-ZSM-5 and tungstosilicic acid. J. Catal. 1993, 141, 308-310.
44. Ballini, R.; Bordoni, M.; Bosica, G.; Maggi, R.; Sartori, G. Solvent-free synthesis and deprotection of 1,1-diacetates over a commercially available zeolite Y as a reusable catalyst. Tetrahedron Lett. 1998, 39, 7587-8590.
45. Kumar, P.; Hegde, V. R.; Kumar, T. P. An efficient synthesis of diacetates from aldehydes using beta zeolites. Tetrahedron Lett. 1995, 36, 601-602.
46. Jin, T. S.; Du, G. Y.; Zhang, Z. H.; Li, T. S. An efficient and convenient procedure for preparation of 1,1-diacetates from aldehydes catalyzed by expansive graphite. Synth. Commun. 1997, 27, 2261-2266.
47. Vijender Reddy, A.; Ravinder, K.; Niranjan Reddy, V. L.; Ravikanth, V.; Venkateswarlu, Y. Amberlyst-15-catalyzed efficient synthesis of 1,1-diacetate from aldehydes. Synth. Commun. 2003, 33, 1531-1536.
48. 2O system. Tetrahedron 2003, 59, 10147-10152.
49. Eshghi, H.; Gordi, Z. Phosphorus pentoxide-montmorillonite K-10 as catalyst for the preparation of 1,1-diacetates under solvent-free conditions. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 1341-1346.
50. Nagy, N. M.; Jakab, M. A.; Konya, J.; Antus, S. Convenient preparation of 1,1-diacetates from aromatic aldehydes catalyzed by zinc-montmorillonite. Appl. Clay Sci. 2002, 21, 213-216.
51. 3+-montmorillonite. Synth. Commun. 1998, 28, 4665.
52. 3 catalyst. Synth. Commun. 2000, 30, 3913.
53. A11 mechanism in hydrolysis of benzylidene diacetates. J. Chem. Soc. B 1970, 1201-1207.